‘Gilmore Girls’: Lorelai Would Have Had a More Successful Career Had She Stayed With Jason Stiles

It is hard to imagine any Gilmore Girls fan not rejoicing when Lorelai (Lauren Graham) and Luke (Scott Patterson) finally got together at the end of the series and eventually marry in Gilmore Girls: A Year in the Life. However, some fans have pointed out that, in many ways, Lorelai’s old flame, Jason Stiles, was an even better match for Lorelai than Stars Hollow’s favorite grumpy diner owner. 

It’s likely if Lorelai had stayed with Jason, she would have had a more successful career.

Who was Jason Stiles in ‘Gilmore Girls’?

The son of Floyd and Carol Stiles, Jason (played by Chris Eigeman) comes from an esteemed family like the Gilmores. His father worked closely with Lorelai’s father, Richard (played by the late Edward Herrmann), in the insurance industry. Jason then makes an unprecedented move upon Richard’s forced retirement and leaves his father’s firm to start a business with Richard.

This is what brings Jason into Lorelai’s life in Gilmore Girls season 4, but their history goes back much further as their families have been close relations since Lorelai and Jason’s childhood (hence their nicknames for each other: “Digger” and “Umlauts.” 

Lorelai would have been more successful had she stayed with Jason

Lorelai and Jason’s relationship comes to an end when Richard Gilmore and Jason’s father, Floyd, strike a deal that cuts Jason out of both of their insurance agencies and threatens to cost Jason his career. In response, Jason sues Richard at the end of Gilmore Girls season 4.

Lorelai is devastated, saying she cannot be in a relationship with someone who is suing her family, and the ordeal further complicates Lorelai’s relationship with her parents. Meanwhile, Luke takes advantage of the situation and finally begins making his feelings known to Lorelai, which leads to the two to finally get together.

However, had she stayed with Jason or had he dropped the lawsuit, Lorelai would have had a much different life and, possibly, a much more successful career. There’s no doubt Lorelai was extremely successful, having worked her way into management and built a business, but there’s also no question she could have done more.

Since Jason was ambitious and hardworking, just like Lorelai, he likely would have pushed her to constantly pursue more for herself. Luke often resisted Lorelai’s ambitions, like when he was hot and cold about encouraging her to sell the inn or take a consulting job in season five.

There’s also a chance Lorelai would have left Stars Hollow and either traveled the world with Jason or set up life in a bigger city. While Lorelai loved the Dragonfly, there was always part of her that pictured traveling the world for business and having influence, similar to what she watched her father do growing up. It’s also unlikely someone who liked luxury and cosmopolitan amenities like Jason would stay in a small town.

However, by the time the two split, Lorelai had just opened the Dragonfly Inn. It was out of the question for her to leave the inn she worked so hard on for so long. While Jason was as ambitious as Lorelai, he wasn’t the type to take the back seat to his partner’s career.

There’s also the fact that while Lorelai felt a pull to some of the things her parents’ life set her up for, like success, influence, and money, she was content with what she built herself. Lorelai found a family in the Stars Hollow community and built a successful business all on her own — and years later, expanded it without the help of any man.

Jason and Lorelai were a surprisingly good fit

As many fans have pointed out, Lorelai and Jason were a great match. Unlike Christopher, who was from high society but relished in the entitlement of it all like a spoiled rich boy, Jason was prepared to work hard for what he got. So much so that he left his secure position as the inheritor of his father’s company to build something of his own—exactly like Lorelai. 

And unlike Luke, Jason knew what it meant to come from the world of the Gilmores. He may have bent the rules, but he knew what the rules were and how to operate within the elite’s code. Luke, on the other hand, scorned the rules of the Gilmores’ way of life and was content with a simple life in Stars Hollow at the diner.

Jason, in large part, fulfilled both sides of Lorelai in a way that Christopher and Luke did not. In a recently-formed forum on Reddit based on unpopular Gilmore Girls relationship opinions, one fan says, “I love Lorelai and Jason!” The user continues, “in some ways, he was exactly like her – off-centre [sic] but from the Gilmores’ world… They really were equals.”

Others claim that Jason was Lorelai’s most “mature” relationship. And while this all may be true, Lorelai and Jason were not meant to be.